The purpose of this study was to identify characteristics associated with bilateral ruptures of the distal biceps tendons. We present a retrospective case series of 25 patients who sustained non-simultaneous bilateral distal biceps brachii tendon ruptures that were repaired surgically, with follow-up available on 10 patients. The average age of the patients was 50 years (range 28-76). All patients were male. The mean time from the first tendon rupture to the contralateral tendon rupture was 2.7 years (range 0.5 - 6.3). Follow-up averaged 45 months (range 24-85). Patients with bilateral ruptures tended to be middle-aged men, who commonly participated in weight lifting, manual labor, or sports, and who had higher rates of nicotine (50%) and anabolic steroid use (20%) than the general population. After surgical repair of 9 of 10 patients, patients with bilateral distal biceps tendon ruptures had good to excellent outcomes. With the numbers available, outcomes were not statistically associated with manual labor, past medical history, prescription medications, prior tendon injury, body mass index, current activity in sports, use of nutritional supplements, or anabolic steroid use, although worker's compensation claims approached statistical significance (p = 0.059). Patients who sustained bilateral distal biceps tendon ruptures tended to be middle-aged men with higher rates of nicotine and anabolic steroid use than the general population.